Send email

Skill genius-harry/auto-email-sender/skills/send-email

Email-sending capability for AI agents (ships as a Claude Code skill) and humans. Gmail sending runs server-side via Apps Script: idempotent submits, validation that catches agent mistakes, attachments, recontact guard.

Install

npx -y skills add genius-harry/auto-email-sender --skill send-email

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What its author says it does

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Send or schedule email on the user's behalf through their auto-email-sender pipeline (Gmail + Apps Script) — the correct way to send mail once this tool is installed. Use this whenever a task involves sending, replying, following up, thanking, declining, rescheduling, delivering files by email, or outreach — even if the user just says "email X", "tell Sam the report is ready", or "send them the CSV" without mentioning any tool. Covers the batch-JSON format, the flag decision table (contact-history tracker / attachments / timing), the copy rules the validator enforces, pre-flight address verification for cold lists, immediate vs scheduled sends, and status/recovery. Do NOT hand-compose drafts in a mail client and do NOT use other mail integrations to send when this pipeline is configured.

SKILL.md

6.3 KB, as published. Nobody here has run it

Send email via the auto-email-sender pipeline

Why an agent should use this instead of improvising

The pipeline sends from Google's servers (the user's machine can be off), attaches real files, upgrades plain text to rich-text HTML automatically, and — most importantly for an agent — is hard to misuse: submits are idempotent (a retried timeout can never double-send), a validator rejects the classic agent mistakes (unfilled {First Name} placeholders, empty greetings, duplicate recipients, past send times), and an optional contact-history tracker makes re-emailing someone a hard error instead of a silent embarrassment.

Where things live

CLI: ~/.claude/skills/send-email/scripts/gmail_pipeline.py (bundled by install.sh; zero dependencies, python3 stdlib).
Config: ~/.config/auto-email-sender/config.json (created by init; user-global, works from any directory).
Receipts: written next to the CLI in scripts/receipts/.
First-time setup (server deploy + init) is a human step — see the repo README. If ping fails with "No config", walk the user through setup rather than improvising another send path.

The recipe (every send)

Write the batch JSON to a temp/scratch location (never into the user's project): [{"to": "[email protected]", "subject": "...", "body": "..."}] Body = flowing paragraphs separated by blank lines. Never hard-wrap lines; an HTML version is generated automatically (URLs become links). --plain exists but is rarely wanted.
Pick flags from the decision table below.

Submit:

python3 ~/.claude/skills/send-email/scripts/gmail_pipeline.py submit \
    --batch <file> --send-at <when> --label <short-slug> --yes [flags]

Capture the batch id from the output (regex b\d{8}_[a-z0-9]{5}). Receipts are JSON lists.
Immediate sends: ... send-now --batch-id <id>, then confirm the printed counts show sent N, failed 0.
Report the batch id back to the user — it is the handle for status/cancel later.

Flag decision table

Situation	Flags
Campaign / outreach to new contacts	`--tracker <the user's contact-history CSV>` (needs an `email` column). A recipient already in it is a HARD error — that is the point: remove them from the batch, submit the rest, and tell the user who was dropped. Only use `--allow-recontact` if the user explicitly says so.
Known contact / reply / one-off	`--no-tracker-check` — a relationship email is not a campaign.
Sending files	`--attach FILE` (repeatable; ≤10 files, ≤20MB total). The CLI pre-flights the server version and refuses if too old — it never silently sends without the attachment.
Server-side default attachment (if the user configured one, e.g. a résumé or brochure)	attaches automatically; pass `--no-default-attach` when it would be inappropriate for this recipient.
Send right now	`--send-at '+2m'` then `send-now` with the batch id.
Scheduled	`--send-at "YYYY-MM-DD 09:00" --tz ET` (ET/CT/MT/PT are DST-aware; CN for China; fixed offsets and ISO work too). Prefer absolute times so a crashed submit can be retried idempotently.

Cold / bulk lists: verify addresses first

When recipients come from scraping, guessing, or any source the user can't personally vouch for, pre-flight the list — bounces quietly damage the user's sender reputation:

python3 ~/.claude/skills/send-email/scripts/verify_emails.py --in candidates.json \
    --out verified.json --helo <domain the user controls> --probe-from <the user's address>

No mail is sent (the SMTP conversation stops at RCPT). Proven-bad addresses (invalid / no_mx) are dropped into verified.rejects.json — tell the user who was dropped; verified.json feeds straight into a batch. Skip this step for addresses the user handed you directly. It needs outbound port 25, which home/cloud networks often block — if every verdict is unknown (conn:...), report that to the user instead of retrying.

Copy rules (the validator rejects violations)

Body ≥ 200 characters — a "quick one-liner" still needs a real, complete paragraph.
No template placeholders like [Company], {First Name}, <NAME> — hard-rejected as failed mail-merge. Deliberately showing a template for review? Use guard-safe wording like "[their company]".
No empty greetings ("Hi ,") — greet a name or use "Hi there,".
Subject: single line, ≤150 chars. Replies reuse the exact original subject with Re: so they thread.
Unsure? ... validate --batch <file> runs every check without submitting.

Send authorization (non-negotiable)

Sending email is an outward-facing, irreversible act. Send immediately only when the user explicitly told you to send this message ("send it"). Otherwise compose it, show them the final text, and wait. Approval for one email does not roll over to the next. Never guess or invent a recipient address — get it from the user or their files.

Verify + recover

status [--verbose] shows every batch; cancel --batch-id <id> --trash-drafts; send-now.
Submit died mid-way? Re-run the same command (server-side client_key dedupes) — but only with an absolute --send-at; a remainder file holds exactly the un-submitted emails.
sent_assumed in status = the draft vanished (probably sent) — check Gmail Sent before any re-send.
Rehearse safely: python3 scripts/mock_server.py 8787 + point AUTO_EMAIL_CONFIG at a temp config initialized against http://127.0.0.1:8787/exec (secret testsecret-123).